Defensive publication

ABSTRACT

5-PYRAZOLONE COLOR COUPLERS ARE INCORPORATED IN ALDEHYDE FOREHARDENED COLOR PHOTOGRAPHIC EMULSIONS AS ENOL ESTERS OF CARBOXYLIC AND SULFONIC ACIDS TO PREVENT REACTION OF 5-PYRAZOLONE WITH ALDEHYDE FOREHARDENING AGENT. A METHOD IS ALSO PROVIDED FOR THE CONVERSION OF THE ENOL ESTER TO THE FREE 5-PYRAZOLONE IN ORDER THAT IT CAN COUPLE WITH OXIDIZED COLOR DEVELOPER WHICH COMPRISES TREATING THE 5-PYRAZOLONE ENOL ESTER WITH AN ALKALINE SOLUTION CONTAINING AT LEAST ONE ORGANIC AMINE PRIOR TO OR CONCURRENT WITH COLOR DEVELOPMENT. ENOL ESTERS USEFUL WITHIN THE SCOPE OF THIS INVENTION ARE ILLUSTRATED BY THE GENERAL FORMULAE:   WHEREIN R REPRESENTS HYDROGEN, ALKYL, THIOCYANO, ACYLOXY, HETEROCYCLOXY, ARYLOXY, ALKOXY, SULFO, ARYLAZO, AMINOARYLAZOXY, ARYLTRIAZOLYL, ALKYLMONOTHIO, ARYLMONOTHIO AND HETEROCYCLICMONOTHIO; R1 REPRESENTS HYDROGEN, ALKYL, ARYL AND HETEROCYCLICF R2 REPRESENTS HYDROGEN, ALKYL, ARYL, HETEROCYCLIC, AMINO, CARBONAMIDO, SULFONAMIDO, ALKYLSULFAMYL AND ALKYLCARBAMYL; R3 REPRESENTS CARBOXYLIC AND SULFONIC ACID RADICALS AND N REPRESENTS A POSITIVE INTEGER OF FROM 1 TO 8. AMINES SUITABLE FOR TREATING THE ENOL ESTERS INCLUDE HYDRAZINE, 1,1-DIMETHYLHYDRAZINE, PHENYLHYDRAZINE, PYRINDINE, IMIDAZOLE, ETHYLENEDIAMINE, TRIMETHYLAMINETRIETHYLAMINE, 2-AMINOETHANOL AND QUINUCLIDINE.

DEFENSIVE PUBLICATIQN UNITED STATES PATENT OFFICE Published at the request of the applicant or owner in accordance with the Notice of Dec. 16, 1969, 869 0.G. 687. The abstracts of Defensive Publication applications are identified by distinctly numbered series and are arranged chronologically. The heading of each abstract indicates the number of pages of specification. including claims and sheets of drawings contained in the application as originally filedv The files of these applications are available to the public for inspection and reproduction may be purchased for 30 cents a sheet.

Defensive Publication applications have not been examined as to the merits of alleged invention. The Patent Oifice makes no assertion as to the novelty of the disclosed subject matter.

PUBLISHED JUNE 1, 1971 S-PYRAZOLDNE ENQL ESTERS COUPLER PRECUR- SORS IN FOREHARDENED INCQRPORATED- COUPLER (IULOR PHOTOGRAPHIC MATERIALS AND METHOD TO CONVERT SAME T0 FREE S-PYRAZOLONE Dale S. Dallon, Kent R. Rush, llmari F. Saiminen, and

Pan! S. Von Bacho, all of Kodak Park, Rochester,

Filed Apr. 27, 1970, Ser. No. 32,428 int. (3]. G03: 1/40 US. Cl. 96l00 No Drawing. 29 Pages Specification S-pyrazolone color couplers are incorporated in aldehyde forehardened color photographic emulsions as enol esters of carboxylic and sulfonic acids to prevent reaction of 5-pyrazolone with aldehyde foreh'ardening agent. A method is also provided for the conversion of the enol ester to the free S-pyrazolone in order that it can couple with oxidized color developer which comprises treating the S-pyrazolone enol ester with an alkaline solution containing at least one organic amine prior to or concurrent with color development. Enol esters useful Within the scope of this invention are illustrated by the general forwherein R represents hydrogen, alkyl, thiocyano, acyloxy, heterocycloxy, aryloxy, alkoxy, sulfo, arylazo, aminoarylazoxy, aryltriazolyl, alkylrnonothio, arylrnonothio and heterocyclicmonothio; R represents hydrogen, alkyl, aryl and heterocyclic; R represents hydrogen, 'alkyl, aryl, heterocyclic, amino, carbonamido, sulfonamido, alkylsulfamyl and alkylcarbamyl; R represents carboxylic and sulfonic acid radicals and n represents a positive integer of from 1 to 8. Amines suitable for treating the enol esters include hydrazine, 1,1-dimethy1hydrazine, phenylhydrazine, pyridine, imidazole, ethylenediamine, trimethylamine, triethylamine, Z-aminoethanol and quinuclidine. 

